Reactions of 4-(Diethylamino)selenet-2(2H)-imine with Nucleophiles – Synthesis of 2-Methylen-3-oxobutane Selenoamides

Title: Reactions of 4-(Diethylamino)selenet-2(2H)-imine with Nucleophiles – Synthesis of 2-Methylen-3-oxobutane Selenoamides

Volume: 7 Issue: 4

Author(s): Plamen K. Atanassov, Anthony Linden and Heinz Heimgartner

Affiliation:

Keywords: Ketenimines, ring opening, selenet-2(2H)-imines, selenium heterocycles, selenoamides, X-ray crystallography

Abstract: 3-Acetyl-N-(4-bromophenyl)-4-(diethylamino)selenet-2(2H)-imine (5a), which is conveniently obtained from the formal [2+2] cycloaddition of 4-bromophenyl isoselenocyanate and 4-(diethylamino)-3-butyn-2-one, reacts with amines, alcohols, water, and thiophenol to give the corresponding 2-methylen-3-oxobutane selenoamides 7 in good yields via ring opening to the ketenimine 6 and subsequent addition of the nucleophile.

Cite this article as:

K. Atanassov Plamen, Linden Anthony and Heimgartner Heinz, Reactions of 4-(Diethylamino)selenet-2(2H)-imine with Nucleophiles – Synthesis of 2-Methylen-3-oxobutane Selenoamides, Letters in Organic Chemistry 2010; 7 (4) . https://dx.doi.org/10.2174/157017810791130685